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The legendary writer Hunter S. Thompson engaged in countless peculiar activities, likely numbering in the hundreds of thousands. For this piece, we’ve chosen the most extraordinary ones, even by his unconventional standards. Given that this is the man behind Fear and Loathing in Las Vegas and the creator of gonzo journalism, these tales are exceptionally bizarre. So, dive in—but keep in mind, once you start, there’s no turning back.
10. He Fired Shots at His Neighbor’s Home
In 1985, Floyd Watkins, a wealthy millionaire, relocated to Woody Creek in Aspen, Colorado. He purchased Beaver Run Ranch, located near Owl Creek, the residence of Hunter S. Thompson. The two quickly became adversaries. Watkins, who amassed his fortune through a debt-collection business, began fortifying his property with concrete walls and fences, diverting streams for artificial trout farms (much to the dismay of downstream neighbors), and insisting on paving the area’s dirt roads to prevent dust from entering his home. When his demands were rejected, he threatened to replace the county board members if they didn’t comply. To assert his dominance, Watkins even imported Bengal tigers to scare off intruders.
Watkins’ obsessive behavior alienated the Woody Creek community. He faced constant harassment, including threatening calls, property damage, and offensive graffiti (such as a sign labeling his home “Fat Loyd’s Trout Farm”). While it’s unclear how much Thompson was involved, Watkins accused him of poisoning his prized trout.
The conflict escalated when Watkins warned a local resident that he would hire armed guards to protect his property and could eliminate anyone who crossed him without consequences. Thompson, likely hearing of this, retaliated that night. As Watkins sat armed in his car, his mansion was riddled with bullets from a shotgun, automatic rifle, and pistol, fired by an unknown assailant who paused only to reload or switch weapons.
Watkins claimed he chased the shooter, who turned out to be Thompson. Thompson showed no remorse, stating the shooting was a protest against environmental destruction. Later, he bizarrely claimed he was attacked by a rabid porcupine and fired in self-defense. When asked to surrender his automatic rifle, it had been tampered with, making ballistic analysis impossible. No charges were filed.
9. He Skipped the Ali Fight to Search for Pygmies
In 1974, Thompson and his illustrator, Ralph Steadman, were sent to Zaire to report on the Rumble in the Jungle, the historic boxing match between Muhammad Ali and George Foreman. The event, hosted by a flamboyant African dictator and attended by elite journalists, was nearly impossible to access. While Rolling Stone provided their tickets, travel, and lodging, Thompson skipped the fight entirely. Instead, he ventured into the jungle, allegedly searching for Nazi war criminal Martin Bormann and seeking out pygmies to inquire if cobras could devour them. It’s uncertain if he found pygmies, but he did trade with locals for ivory, claiming to be George Foreman’s physician, Dr. Bormann.
After the match, writers George Plimpton and Norman Mailer returned to their hotel to find Thompson naked in the pool, intoxicated and oblivious to the fight’s outcome. The chaos didn’t end there. Upon returning to the U.S., customs seized Thompson’s ivory. Instead of paying the minimal fee (around $60), he bolted past security, leaped over a desk, grabbed the tusks, and fled, pursued by airport officials.
8. He Lit the America’s Cup Ablaze
Another bizarre escapade involving Thompson and Ralph Steadman included a regatta, a luxury yacht, anti-papal graffiti, a flare gun, and a disastrous fire. In a style reminiscent of the gonzo journalism that birthed Fear and Loathing in Las Vegas, Thompson decided to cover the America’s Cup, a prestigious yacht race, bringing Steadman along for illustrations. After renting a sloop to get closer to the action, Steadman noticed Thompson consuming pills, which he claimed were for seasickness. Unaware, Steadman took one, only to discover they were hallucinogenic psilocybin. Soon, Steadman, hallucinating red-eyed dogs, suggested spray-painting “F*** THE POPE” on a yacht.
The duo soon found themselves in a dinghy, attempting to graffiti an expensive yacht. When a security guard confronted them, Thompson panicked, and they clumsily fled back to their sloop. As the psilocybin wore off, Steadman began to panic, realizing the gravity of their actions. Things escalated when Thompson fired a flare gun, with the second shot hitting a wooden yacht, igniting it. Chaos erupted as people scrambled to extinguish the flames and find the culprits. Thompson and Steadman were rescued by a fishing boat and spent the morning in a café, overhearing locals rant about the boat arsonists.
7. He Nearly Killed Bill Murray
In the early ’80s, Thompson frequently spent time with Bill Murray, who had met him after agreeing to portray Thompson in Where The Buffalo Roam. One evening, while drinking, the two engaged in a game of Houdini-style escapes. Confident in his abilities, Murray attempted an underwater rope escape. Thompson tied him to a chair with duct tape and pushed him into a pool. Murray quickly realized he couldn’t escape and began drowning. Fortunately, Thompson rescued him just in time.
This wasn’t the only instance where Thompson nearly endangered an actor portraying him. Two decades later, Johnny Depp spent considerable time with Hunter to prepare for his role in Fear and Loathing in Las Vegas. While staying at Owl Creek, Thompson set up a basement room for Depp. As Depp was about to light a cigarette, he noticed the ashtray rested on a box of dynamite. After hastily extinguishing his cigarette, he discovered the basement was filled with explosives. Hunter later explained the dynamite was for bomb-making, adding, “If you’re baking a cake, you’ll need flour.”
6. His Strange Interview with Keith Richards
What occurs when an unstoppable force collides with an immovable object? If the force is Keith Richards and the object is Hunter S. Thompson, we have an answer. In 1993, ABC’s “In Concert” series was promised an interview with Richards during his wildest, drug-fueled phase. However, Richards demanded more money, locking himself in and refusing to cooperate. ABC, opting for a bold solution, enlisted Thompson to conduct the interview. Hunter agreed but faced the issue of the locked door. He resolved it by playing a recording of a pig being slaughtered through a megaphone, blasting it at the door until a confused—and armed—Richards opened up. The interview, available above, begins with Thompson’s line: “Hi. My name is Hunter S. Thompson, and I haven’t been paid yet.”
5. His Birthday Present to Jack Nicholson: Elk Hearts, Blinding Light, and Gunfire
Another of Thompson’s famous acquaintances was Jack Nicholson. The two had developed a tradition of exchanging bizarre gifts. For Nicholson’s birthday, Thompson decided to deliver an unforgettable celebration. Arriving after dark, Thompson climbed a ridge overlooking Nicholson’s home and ignited a 40-million-candlepower parachute flare, illuminating 40 miles of darkness with a glow resembling “the initial flash of a nuclear explosion.” He then directed a million-watt spotlight at the house, blasted his infamous dying pigs recording through a loudspeaker, and fired his automatic pistol into the air.
Jack Nicholson did not step outside.
Unbeknownst to Thompson, Nicholson was already on edge due to a deranged stalker. When no response came to the gunfire, blinding light, sky explosions, and horrifying sounds, Thompson left a fresh elk heart on Nicholson’s doorstep, feeling slighted by the lack of acknowledgment.
4. He Befriended Richard Nixon
If Hunter S. Thompson had an arch-enemy, it would undoubtedly be Richard Nixon. Thompson had spent years attempting to discredit, infuriate, and dismantle Nixon’s career. He even vowed to leave the U.S. if Nixon was re-elected (he was, and Thompson stayed). His disdain for Nixon was palpable. However, while working on Fear and Loathing on the Campaign Trail, something unexpected occurred. Thompson secured an interview with Nixon himself. Though brief—just a car ride to the airport—it had the potential to become historic, akin to the Frost/Nixon interviews.
What transpired? Did Thompson solidify his reputation as a top political writer by dismantling the man he blamed for the nation’s woes? Not quite. Instead, he found himself engaging in a cordial discussion about football with his longtime adversary. Whether Nixon even recognized Thompson remains unclear, but Hunter described the odd exchange as akin to chatting with an old friend.
However, this being Thompson, there was one incident that alarmed Nixon’s security. When the car stopped for gas, Thompson stepped out, lit a cigarette, and nearly caused an explosion. Despite the strange camaraderie during the ride, Thompson later described Nixon as possessing an “ugly, Nazi spirit” in his obituary.
3. He Ran for Sheriff
In 1970, Thompson embarked on one of the most unconventional political campaigns in history, running for Sheriff of Pitkin County, Colorado. Backed by the “Freak Power” movement, he represented the counterculture of the late ’60s, opposing incumbent Carol Whitmire. Thompson’s platform included legalizing recreational drugs (while punishing unethical dealers), tearing up roads to replace them with grass, banning tall buildings that obstructed scenic views, and renaming Aspen “Fat City” to deter developers he called “land rapers.”
Thompson quickly clashed with the incumbent sheriff, who resorted to underhanded tactics, such as threatening to arrest anyone who appeared likely to vote for Thompson. A particularly alarming incident involved the theft of over 200 sticks of dynamite from a local ski company, accompanied by a menacing note threatening to destroy half the county if Thompson won. In response, Thompson shaved his head, mockingly referring to his conservative, crew-cut opponent as “my long-haired rival” during debates. To Thompson’s shock—he never anticipated the race becoming so intense—it seemed he might actually win. To prevent this, Whitmire, a Republican, joined forces with the Democratic candidate to combine their votes. Thompson ultimately lost by a narrow margin of four percentage points. Had a few more votes swung his way, Aspen might now be known as Fat City.
2. He Aided in Freeing a Wrongfully Convicted Woman
In 1998, Lisl Auman was sentenced to life in prison for the murder of a police officer, despite being handcuffed in the back of a patrol car at the time of the shooting. According to the official account, Auman was riding with an acquaintance when they were stopped by police. She was handcuffed and placed in the squad car, while the driver shot the officer and then himself. Under felony murder laws, Auman was held responsible and given a sentence of life without parole, even though she had no direct involvement in the crime.
It seemed she would remain imprisoned for life—until Thompson stepped in. After receiving a letter from Auman, he was so outraged that he launched a nationwide campaign to highlight her case. Leveraging his connections, he enlisted celebrities like Benicio Del Toro, Johnny Depp, and Jack Nicholson, tirelessly advocating for her freedom. After seven years in prison, Auman was acquitted and released. Sadly, Thompson passed away earlier that year and didn’t witness her freedom. Auman remains free, and her story is set to be adapted into a Hollywood film.
1. Being Assaulted by Hell’s Angels
In 1966, Thompson’s debut book, Hell’s Angels: The Strange and Terrible Saga of the Outlaw Motorcycle Gang, was published. To research it, he spent two years living with and observing the Hell’s Angels, often terrified by their actions. Initially, the relationship was cordial, and Thompson provided an unprecedented look into their world, seemingly unfazed by the violence he witnessed. However, things changed when he saw an Angel named “Junkie George” delivering a savage beating to his girlfriend.
During the attack, George’s dog bit him, prompting him to turn on the animal. Disgusted, Thompson intervened, declaring, “Only a punk beats his wife and dog.” This led to a brutal assault by Junkie George and the other Angels. They knocked him to the ground, kicking and punching him, with one attempting to crush his skull with a rock—fortunately, it missed. Thompson was hospitalized, and the incident marked the violent end of his association with the Angels. The experience left a lasting impact, as seen in a 1967 talk show clip where Thompson is visibly shocked by the appearance of one of his attackers.
